Emma's Summer Babysitting Job

Hi, this story is my official entry in the 2010 LITEROTICA Summer Lovin' Contest. It's also vying for a prize in the ASSOCIATION of INDEPENDENT READERS contest that runs concurrently.

It's your votes, the votes of readers around the world that will decide the contest winners -- please, after you've read the story, take the few extra seconds required to place your vote.

The sexual encounters described in this story involve only people who are 18 years old and over. Although fictionalized it is based on a true story.

Mid July 2009 Couries Village, Hopkins Island, Massachusetts

"Maaaaatt?"

"Mrs. Pemberton-Smith," I answered with a quick nod of acknowledgment as I handed Emma and her friends a menu each. "Mrs. Connors ... Miz Burton," I added as I looked down at the three twenty something year old women I'd known all my life. I was grinning.

"Matthew Liam Hopkins?" Emma Pemberton-Smith, nee Kruger, said as she jumped up from her seat, the surprise clear in her voice. "What are you doing here?" she asked as she enveloped me in her arms.

"My god it is," Trudi Burton said as I felt the eyes of all three examining me.

"Not little Matty? What happened to you?" Jackie Connors said. She, even at her age and married for four years, was still, with her pixie face, the cutest girl on the island.

Of course I blushed. "Ha, ha. So, all of a sudden I'm that hard to recognize," I finally asked. But I knew there was no way I was going to stop them. They were famous teasers and together in a group were unstoppable.

"Gawd, Mom and Katie said you'd grown up, but not--" Emma started as the girl I'd loved since I was two years old pulled me even closer.

"They didn't say he'd become Mr. Hunk though," Jackie interrupted.

We were on Hopkins Island, an island sitting in the Atlantic, a twenty minute ferry ride from the mainland, an island that was named for a great, great, great, great grandfather of mine and which was famous for the wide pristine beaches that circled it.

Eight miles long by about two wide, it was home to about two hundred permanent residents, most of who lived in the small port of Couries, and who lived off the tourists who flocked there every summer.

People like my family, and Emma's and Trudi's and Jackie's, who'd descended from the earliest owners, and who now owned ninety percent of the three hundred some cottages that were sprinkled along the shoreline. People who spent most of the year in Boston or New York or Philadelphia, but who each summer flocked back to the island. We were a group of families who'd intermarried extensively in the early pioneer days before dispersing out into the bigger world. Emma and I had figured out years before, using old genealogy tables one of my great aunts had collected, that we were fourth cousins once removed.

The three girls I'd just handed menus to I'd known all my life. Six or seven years older than me they'd been part of the landscape of my summer months for my first sixteen years.

Emma, our closest neighbor, had become my babysitter whenever mom had needed one in those long ago years. But she'd been even more than that. The fact that my mom, still a teenager, and only nine years older than Emma, a girl she'd looked up to all her life, had mothered a child was an irresistible lure to the young girl who lived two hundred yards down the beach.

She'd become a part of our little family. Mom and Emma and I. Emma had spent as much time in our kitchen cooking pies with mom as she had looking after me.

"Gawd I've missed you soooo much," Emma said as she gave me another hug. I inhaled her presence even as I felt her breasts against my chest; she was the girl who'd always smelled better than any other. She'd been holding me in her arms since I'd been a week old.

"Hah, you shouldn't have run off and married that--"

"Ooooohhh Matty, if only you'd been a little older," Emma cooed in my ear before releasing me. Her friends laughed. I smiled, but not inside.

As I served the three of them their drinks and lunch we all caught up to date on each other. Where we were living, school details, marriage status, babies etc., etc. It was something that happened a thousand times between returning islanders in those first days back on the island each summer. A trading of news and gossip that caught us up on people we hadn't seen since the year before.

"What are you doing here anyway?" Jacqui finally asked. Instead of admitting that I was doing a favor for my girlfriend, the daughter of the restaurant's owner, I just told them that a friend had asked me to fill in for him for one shift.

"Are you going to be staying out on the island all summer?"

"Yeah, mom's given me a hundred jobs to do around the cottage."

"How is your mom?" Emma asked.

"She's working ... she'll be here this weekend."

"Clark too. But tell your mom I'll be over to your place Saturday morning, first thing," she promised. "And you too. I want to see you, we have so much to catch up with. Come to the beach tomorrow," she insisted as she looked up into my eyes. I nodded. "Promise?"

The Next Day

"Hey," I said when I'd gotten within ten feet of her. She was sitting in a beach chair, her toes dangling in the breaking surf. I'd been walking towards her with the sun at my back.

"Hey you," she answered back when she finally recognized me.

I was eighteen. Emma twenty-five. She was wearing a skimpy yellow bikini. There wasn't one girl on the island who'd have looked better in it.

"You shouldn't be allowed out in that," I told her as I sat down on the towel next to her.

"Why not?" she asked. Meanwhile she slowly arched her back in a languorous stretch that tested, almost to the breaking point, the strength of the clasp that held the bra together. I was surprised by her pose, although I'd seen her flirt before, the big difference in our ages, and our relationship -- young boy and babysitter -- had precluded any sort of even mild sexual interaction between us in the past.

"Twenty-five year old married women shouldn't be teasing poor little innocent thirteen and fourteen year old boys. You might just ruin them for life," I teased as my eyes flicked over the body in front of me.

"I don't see any fourteen year old boys." She let her eyes drift down over me as she said the words.

"Their mothers have locked them all up."

"I didn't ruin you for life when you were thirteen," she challenged as she unconsciously moved into another pose that highlighted her body.

Little did she know I thought to myself. "You're still the most beautiful girl on the island."

"Yeah right." Emma's eyes were shining.

"I've missed you. Gawd I've missed you," I told her as I let my hand rest on her knee for a second.

"It's too bad you're still not seven years old. Clark and I would baby sit you any time your mother wanted."

"So you don't approve of the eighteen year old model?" I asked.

"The eighteen year old model is more than just fine," she answered with her nicest smile. "In fact he's pretty darn handsome."

"You should have waited."

"I should have ... but I was swept off my feet ... by the sexy and debonair Mr. Pemberton-Smith ... how could I refuse?"

"Yuck! By the way, how is the wonderful Clark these days?"

"Don't be a bad boy Matty," she admonished. We were teasing. We both knew each other too well. But there was something new, something that had never been there during our first fourteen years together. And it was directly related to the part of my anatomy that was rapidly stiffening in my shorts. It had never been part of our relationship before.

"Yeah and apparently I've got to play mister debonair in the semi-finals of the club championship this weekend."

"I know. He's so excited," his wife answered. "He's wanted to win it for years. You should have heard him when he won his last match. I've never seen him so happy."

What an asshole I thought. Fuck, this guy's married to a goddess and the best moment of his life is winning a quarter-final match in the Hopkins Island Country Club's Championship. "He doesn't have a chance," I boasted. I wasn't planning on letting Clark Pemberton-Smith, a lawyer for crying out loud, beat me. Not now that I'd seen Emma again.

"That's what daddy told him."

"Your father told Clark he couldn't beat me?" Emma nodded yes. I laughed. I'd always liked Emma's old man. "That must have made his day."

"Daddy said he played with you a couple of weeks ago and you looked unbeatable."

"I'll bury poor old Clark."

"Don't you dare! You should let him win, it's only fair. You're younger; you'll have lots of other chances."

"Are you saying you really want me to let Clark win?"

"Yes you should. For me. For all I did for you." The challenge, the calling in of long ago earned IOU's was clear in her voice.

I swallowed the quick refusal that had rushed to my lips. Then thought a second. Then decided. "Okay, if you ask me I will," I invited.

"A whole pie just for a silly golf game?" she asked in a tone that said, 'are you nuts'. But then she started to laugh. Then she leaned over and gave me a quick kiss on my lips. Not quite a boy/girl kiss but somehow more than a babysitter or brother/sister one.

"So does mean we've got an agreement?" I asked.

"Yes, but it's going to be an Emma Pemberton-Smith pie," she said as she jumped up and ran laughing into the surf. "And don't you dare tell him," she yelled back.

"It wasn't a very good kiss," I complained as she dove into the waves.

I was in love again. And that was before she came running out of the surf, with droplets of water flying off her athletic body, with her breasts straining as they jiggled, with the darkness of her aureole showing through the thin yellow material, with her long curly blond locks dancing in the sunlight ...

... and then she threw herself down onto her back next to me on the beach towel. "I LOVE THE SUMMER," she yelled to me and the gods above as she spread her arms and legs in an invitation to the sun to ravish her. The clearly outlined camel toe of her sex was the only invitation I watched.

"Shall I cream you?" I asked as I reached for the tube of lotion.

"Just you remember Matty Hopkins that I'm a married woman."

"Yes ma'am," I answered as I squeezed the tube.

I spent about two hours with Emma on the beach that day. I creamed her front and then later her back. She did the same for me. And it wasn't like it was when an eleven year old Emma Kruger had put sunscreen on four year old Matty. And we both knew it.

We swam. We laughed. We remembered. And for the first time we flirted. And there was absolutely no doubt in my mind that she knew what effect she'd had on me. Or that she'd enjoyed it.

But Emma Kruger was now Mrs. Clark Pemberton-Smith. But as I walked home that afternoon I knew that it didn't matter... I knew I wanted her more than any young boy ever had ...

GOLF Sunday, July 19th

Clark Pemberton-Smith wasn't that bad a guy. Or so everyone said. The prick!

Like Emma I'd known him all my life. Like Emma and I, he too was a descendant of one of the original families. He was three years older than Emma and close to ten older than me. I'd seen him on the beach, at parties, out sailing, throwing a football on the beach and everywhere else on the island all my life. He'd even been a day camp councilor for the younger kids, including me, when he was seventeen or eighteen.

I didn't like him. Never had. Well maybe that's not true. Maybe I only started disliking him when he started hanging around Emma. I'd known nothing about the whole sex thing of course. What seven or eight year old boy does? But somehow I'd sensed that Clark was up to no good with my baby sitter, with my friend, with my almost sister. I didn't know how or why but I knew he was a danger to her. And hence to me and mom.

Of course he really wasn't! He was just a horny teenager who all of a sudden had realized that the young girl, some three years younger than he, had all of a sudden become the prettiest and most desirable girl on the island. Something every other guy had realized at about the same time. Honestly, looking back, I only disliked him because it was his interest that Emma returned.

It really wasn't until Emma was sixteen or seventeen that they started to go out as a couple. And of course that just ratcheted up my dislike of him even more.

And Clark knew I didn't like him. I'd overheard him talking to Emma once, when she was eighteen or so, when he'd asked her, "What is with that little prick, every time I come over he--"

"Almost brother! He's a jerk. Christ, did you see him, his little hands curled into fists the second I came into the room. It's like he's trying to protect your honor."

"And what's wrong with that?" Emma asked.

I was eleven that summer, Clark was twenty-one.

Emma married him three summers later. By that time I'd come to understand what I was losing. She danced with me at the reception. And in her white gown and with her shining, happy eyes she'd broken my heart. Late into that night, hours after the reception had ended, I'd sat crying in my mother's arms on the beach that fronted our summer home.

***

Clark called me on the following Friday night, right after he'd arrived on the island ferry, to arrange the match. Sunday morning at nine a.m. was arranged. And as I biked over to the islands golf course on that Sunday I was still debating with myself if I should let him win. And my indecision had grown even greater after we'd played nine holes.

"You don't have to do it you know," Emma said to me seconds after her husband and I had finished the front nine.

"Don't have to do what?" I asked back.

"He shouldn't have said that." Even though he was a pretty good player, in fact he was a good all round athlete, Clark was one of those guys who gets nervous on the golf course. And when he got nervous he talked. And that day he talked to his golf ball, to his clubs, to the five or six people who were following us around, and of course to me. He was big time nervous!

It turned into one of the least enjoyable nine holes I'd ever played. And it had ended with him saying, as we were walking over towards the snack hut, that maybe it would be better if I just conceded now. 'Hell, why waste any more time kiddo, once I get ahead I'm unbeatable'.

I had let him win the ninth to go one up. Even Emma had cringed when she heard his words.

"Clark just can't help himself," I told his wife.

"I'm just saying I won't hold you to our deal."

"A deals a deal," I answered. "Besides, I already collected part of the price."

"It doesn't matter." I could see that Clark's talking and boasting had bothered her more than it had me.

"So do you want the kiss back then?" I then pursed my lips and kissed the air.

"You're crazy." There was a wry smile on Emma's lips.

"I'm still going to let him win ... but my price has gone up," I added, then turned and started towards the tenth tee.

"Gone up where?" I heard behind me.

I kept the game close. In fact I was one up after fourteen. I let him win the sixteenth so we were even with two to play. He cheated on the seventeenth hole! The fucker actually cheated. He thought he'd got away with it without anyone seeing him. But, from twenty yards away I'd spotted it when he'd nudged his ball with his foot and turned a horrible lie in the rough into a good one. Emma saw it too. I could see she was going to protest, even call her husband out on it, but before she did, I shook my head no.

We halved the seventeenth and so went to the final hole even. A final hole on which Clark, in spite of a case of nerves that caused him to bogey the hole, won the match when I, who seemingly choked, took four to get down from a greenside bunker and handed my opponent the victory.

Clark couldn't stop from crowing when my putt slid by on the high side. And he couldn't help announcing to the crowd that had gathered around the eighteenth green that this brilliance and experience had carried him easily to victory over the callow Hopkins boy. 'The young pup's still got some growing up to do', Clark announced as he escorted me from the green.

Emma couldn't meet my eyes. She knew that the young pup wasn't happy.

Thursday July 22nd The Pond

"Guess what I brought besides the promised pie," my favorite married woman asked me as she dismounted from her bike and leaned it against the side porch. She was wearing a pair of tight orange shorts and had unleashed her long blond curls; they seemed to be dancing as they trailed down her back. Her full, high breasts were straining against the white bikini top that was attempting to hold them in. She had come to pay her debt.

"Your infamous beauty?" I suggested.

"Ha, ha," she answered as she grabbed the hamper from her bike basket and walked towards me.

I just had on a pair of cut-off jean shorts. I'd been splitting logs for the woodpile when she'd pulled in and the sweat was pouring off me.

"You're sweaty, you've got all sorts of little pieces of bark and wood on you," she said, then gingerly leaned in and quickly plucked a couple of wood chips off my chest.

"You missed some," I answered. I'd have willingly stood there and led her pick stuff off my body all day.

"Do you want to eat now or swim first?" she asked.

"C'mon, we'll go have lunch at the pond, I'll wash there," I said as I took her hand.

Mom's end of the island, an piece of land inherited from her grandfather to the chagrin of many other family members, had only a modest cottage on it but did have its own pond, one of the few on the island, as well as, due to its location, almost complete privacy. The most valuable piece of real estate on the island, it had been left to the unmarried mother who'd had a child out of wedlock when she was sixteen years of age. A granddaughter who'd been nurtured by her loving grandparents after her parents had rejected her. The land, and a relatively large trust fund, had then been left to mom when they'd died in a tragic car accident when I was only four.

Emma Kruger was no stranger to the pond. In fact, besides my mom and I, she was the only person on the island who'd had free reign of the Hopkins acreage over the years. We'd spent a hundred afternoons there during my boyhood.

"He was an ass, he shouldn't have said those things," Emma said as we walked hand in hand through the copse that rose just west of the cottage.

"He cheated," I accused. "That'll cost you," I threatened.

"That's why I brought sandwiches too."

"Hah! Sandwiches? You're going to have to do better than that," I snorted as we broke through the last of the dense foliage and found ourselves in a sun filled glade about a hundred yards in diameter. The pool, fed by a trickling creek, was surrounded on all sides by a ring of wild, waist high summer flowers.